When You’re Heading Out

Sometimes the things they say on packaging can be hilarious in way-overkill fashion. Sometimes it can be spot on. The box of the cereal I’ve been munching on states, “What matters most is what’s inside.” It’s true for cereal boxes and people and it’s been making an impression on me lately.   

Photo by Katrina Keyes
Photo by Katrina Keyes

My little sister left home yesterday. Not home where I live, but my original home far away–the place I resided before I made that big move and started the journey I am still on. She started her own journey, and such journeys are always in need of thoughtful words. Our family has a tradition. “Plane letters” we call them.

Nobody gets on a plane without letters. I have received more than my fair share of plane letters, because I’ve gotten on more than my fair share of planes! But yesterday was my sister’s giant day–the kind that only comes once–and her turn for a plane letter or two. It’s was hard for me not to be there at that big gate with the rest of my family. I knew what they would do. I knew they would check her in, take her upstairs, and sit down at a little table. People with perfectly good mouths and senses of humor would have no idea what to say. All words are inadequate at plane gates. And then there’s that time when you pile up against the security checkpoint–the one with the wall that you can’t see past. It’s the final point where you have to say goodbye and one person’s wondering what in the world they’re doing, and everybody else is wondering what the world will look like with that extra hole. This is where the plane letters come out and press their way into uncertain hands, accompanied by weak smiles and tears.

I was thankful there were two sheets of paper from me pressed into hands I love that day, even if I couldn’t stand there with the tears. I wrote my letter and sent it home to be sent out in the world with my sister. And what I wrote, I wrote because I know it’s what a soul making that journey needs to hear. I know this because I still need to hear it. It’s the words I needed then, and the words I still need now. Words to remind me that “what matters most is what’s inside.” These are some of those words (edited), because if I could, I would write such a plane letter to every person starting a journey. Michelle you are beautiful! Thank you for letting me share your letter.

To my Darling Sister,

I cannot believe that this is happening in your life. But then, I can’t believe anything of what’s happening in my life either, so I suppose that is to be expected! It’s so cliché to say that it “seems like yesterday” we were blah blah blah. But it’s so true. I still stop, look around me and think, “how on EARTH did I end up here, and what exactly am I doing?” Just putting one clumsy foot in front of the other it seems at times! 

We love the power of reason. We love to reason out our lives and our decisions and make the best possible ones we can. There’s a lot of merit in that. A lot of merit to making good choices. But sometimes it’s a smoke screen barely hiding the fact that we don’t really know what we’re doing. It’s a pretense at controlling life. So while there are some good decisions and some bad ones, there is no perfect reasoning through which we can make the perfect decisions and secure the perfect life. A good deal of life is happenstance and uncertainty. A good deal of life is plan Bs and navigating with half vision. But it’s the internal works that count. Success, in one of its most meaningful definitions is the health of our heart. It’s not so much the life we live as how we live it and how we allow it to shape us.

Every time we step out in the daily and in the momentous to make something in the world, we are making something within—a reality of the heart. We can focus so much on what we make out there that we know nothing of what we have made in here. And that’s the real treasure. That’s where it counts.

This is a big moment for you. You’re leaving home for the first time. You’re done with college. It’s the moment when you don’t know what you’re doing or whether it even matters or not. It’s the moment when you sense that now the world really expects something of you. It’s the moment when I’m sure you will be relieved to head out on your own feet, but distrustful of the path you’re walking. You’re likely to get lonely and confused. But it’s a glorious moment. It’s a moment when you get to define your own person, explore, choose, walk.

If I could tell you anything, I would tell you not to spend your time wondering about the path you’ve chosen. Don’t deliberate about whether it’s the best one, where it will lead, and how other paths would have perhaps led to places much better. Don’t waste your energy telling yourself how pointless it is or how much of a mistake you’ve made. Don’t waste your precious emotions and heart trying to manipulate and control and understand life. Instead, make choices about how you will engage with today. Every today. Don’t look only at what you are building (or not building) around you, but look at what you’re building inside. How have you greeted today? Did you make choices from a value for who you are? Because then, if you wake up in the morning and you do that, you will have a great day. A day in which you built something that counts. And then, by the end of your time, regardless of whether you have connections or promotions or a clear road to head out onto next, you will have something completely yours. You will have the internal resources to face your next uncertain road. You will have invested in you.

Enjoy the dare of it all. You’re going to be ok! 


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